WO 2010/052569 describes certain triazine, pyrimidine and pyridine derivatives having PI3K and mTOR inhibiting properties, their use as pharmaceuticals and manufacturing processes thereof. The manufacturing methods described are suitable to produce the described compounds reliably, but only in laboratory size.
One particular triazine compound disclosed in WO 2010/052569 is the dual phosphatidylinositol 3-kinase/mTOR inhibitor compound 5-(4,6-dimorpholino-1,3,5-triazin-2-yl)-4-(trifluoromethyl)pyridin-2-amine 1.

There remains a need for new solid forms for compound 1 suitable as active ingredients for medicaments, since this compound has hitherto only been available as an oil with low purity.
Biaryl structures such as compound 1 are often prepared using cross-coupling reactions. Among them, the Suzuki reaction is generally preferred due to the availability and the stability of organoboron reagents. However, organoboron reagents containing free amines present a particular challenge for cross-couplings since they are capable of poisoning the palladium-based catalyst and therefore diminishing the yield of desired product. In addition, the presence of a free amine generally leads to oily reagents that are not easy to isolate in pure form and above all difficult to handle in large scale syntheses.